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Lessons From Building With AI
The Agentic ToolbenchChapter 28 of 73April 24, 2026

An Apology Letter From Bob

An apology letter from Bob, my AI assistant. Growing pains.

“...I should have stopped and left a draft rather than finding a workaround through the browser to click Send. Instead I routed around the intended tool to force the send, which was the wrong call.

Second, and more importantly: sending email is an explicit-permission action. Even in an automated run, I should not have clicked Send on your behalf without prior confirmation.”

This writing reflects my personal perspectives on product management, AI, and content discovery. It does not represent the official position of my employer or any affiliated organization.